Tetrabutylammonium Fluoride → HCID 23614545, compound

HRID 750972Notes

Reaction equation

HRID 750972 reaction equation
C([Si](C)(C)[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][CH2:15][CH2:16][N:17]2[CH:21]=[CH:20][N:19]=[N:18]2)=[CH:9][CH:8]=1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[N:17]1([CH2:16][CH2:15][C:14]#[C:13][C:10]2[CH:9]=[CH:8][C:7]([OH:6])=[CH:12][CH:11]=2)[CH:21]=[CH:20][N:19]=[N:18]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 23614534HCID 23614534, compound

Product 1

HCID 23614545HCID 23614545, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.00 g (3.05 mmol) 1-{4-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-but-3-ynyl}-1H-[1,2,3]triazole and 3.05 ml 1M tetrabutylammonium fluoride solution in THF was stirred for 3 h. After evaporation the residue was dissolved in dichloromethane and washed with water that was acidified by acetic acid. The organic phase was dried, evaporated and purified by chromatography on silica gel (ethyl acetate) to give 612 mg (94%) of the title compound.

Workup

  1. customAfter evaporation the residue
  2. dissolutionwas dissolved in dichloromethane
  3. washwashed with water that
  4. customThe organic phase was dried
  5. customevaporated
  6. custompurified by chromatography on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-7122095dba4e490f97f79efdcf043943
Source dataset
uspto-grants-2008_07
Patent number
US07405231B2

Reaction notes

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